Bioactive caffeic acid esters from Glycyrrhiza glabra

S. Dey, M. Deepak, M. Setty, P. D'Souza, A. Agarwal, G.K. Sangli

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

Thin layer chromatography bioautography (using DPPH spray reagent) guided fractionation of Glycyrrhiza glabra led to the isolation of two caffeic acid derivative esters, viz. eicosanyl caffeate (1) and docosyl caffeate (2). The two compounds exhibited potent elastase inhibitory activity, with IC50 values of 0.99μg mL-1 and 1.4μg mL-1 for 1 and 2, respectively. The compounds also showed moderate antioxidant activity in DPPH and ABTS scavenging assays. The results indicate a possible role of caffeic acid derivatives, in addition to flavonoids in the anti-ulcer properties of G. glabra.
Original languageEnglish
Pages (from-to)1657-1663
Number of pages7
JournalNatural Product Research
Volume23
Issue number18
DOIs
Publication statusPublished - 2009

Fingerprint

Glycyrrhiza glabra
Glycyrrhiza
caffeic acid
Esters
chemical derivatives
esters
Derivatives
Thin layer chromatography
elastase
Pancreatic Elastase
Scavenging
Fractionation
Thin Layer Chromatography
Flavonoids
thin layer chromatography
Inhibitory Concentration 50
Ulcer
inhibitory concentration 50
Assays
fractionation

Cite this

Dey, S., Deepak, M., Setty, M., D'Souza, P., Agarwal, A., & Sangli, G. K. (2009). Bioactive caffeic acid esters from Glycyrrhiza glabra. Natural Product Research, 23(18), 1657-1663. https://doi.org/10.1080/14786410802134348
Dey, S. ; Deepak, M. ; Setty, M. ; D'Souza, P. ; Agarwal, A. ; Sangli, G.K. / Bioactive caffeic acid esters from Glycyrrhiza glabra. In: Natural Product Research. 2009 ; Vol. 23, No. 18. pp. 1657-1663.
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abstract = "Thin layer chromatography bioautography (using DPPH spray reagent) guided fractionation of Glycyrrhiza glabra led to the isolation of two caffeic acid derivative esters, viz. eicosanyl caffeate (1) and docosyl caffeate (2). The two compounds exhibited potent elastase inhibitory activity, with IC50 values of 0.99μg mL-1 and 1.4μg mL-1 for 1 and 2, respectively. The compounds also showed moderate antioxidant activity in DPPH and ABTS scavenging assays. The results indicate a possible role of caffeic acid derivatives, in addition to flavonoids in the anti-ulcer properties of G. glabra.",
author = "S. Dey and M. Deepak and M. Setty and P. D'Souza and A. Agarwal and G.K. Sangli",
note = "Cited By :11 Export Date: 10 November 2017 CODEN: NPRAA Correspondence Address: Deepak, M.; RD Centre, Natural Remedies Pvt. Ltd., Bangalore, India; email: deepak@naturalremedy.com Chemicals/CAS: 1,1 diphenyl 2 picrylhydrazyl, 1898-66-4; 2,2' azinobis(3 ethylbenzothiazoline 6 sulfonic acid), 28752-68-3; acetic acid, 127-08-2, 127-09-3, 64-19-7, 71-50-1; gallic acid, 149-91-7; methanol, 67-56-1; ursolic acid, 77-52-1; water, 7732-18-5; Antioxidants; Caffeic Acids; Enzyme Inhibitors; Esters; Pancreatic Elastase, 3.4.21.36; Plant Extracts; caffeic acid, 331-39-5 References: Auddy, B., Ferreira, M., Blasina, F., Lafon, L., Arredondo, F., Dajas, F., Screening of antioxidant activity of three Indian medicinal plants, traditionally used for the management of neurodegenerative diseases (2003) Journal of Ethnopharmacology, 84, pp. 131-138; Bafna, P.A., Balaraman, R., Anti-ulcer and anti-oxidant activity of pepticare, a herbomineral formulation (2005) Phytomedicine, 12, pp. 264-270; Beith, J., Spiess, B., Wermuth, C.G., The synthesis and analytical use of a highly sensitive and convenient substrate of elastase (1974) Biochemical Medicine, 11, pp. 350-357; Belinky, P.A., Aviram, M., Fuhrman, B., Rosenbat, M., Vaya, J., The antioxidative effects of the isoflavan glabridin on endogenous constituents of LDL during its oxidation (1998) Atherosclerosis, 137, pp. 49-61; Borrelli, F., Izzo, A.A., The plant kingdom as a source of anti-ulcer remedies (2000) Phytotherapy Research, 14, pp. 581-591; Fukai, T., Satoh, K., Nomura, T., Sakagami, H., Preliminary evaluation of antinephritis and radical scavenging activities of glabridin from Glycyrrhiza glabra (2003) Fitoterapia, 74, pp. 624-629; Fukai, T., Satoh, K., Nomura, T., Sakagami, H., Antinephritis and radical scavenging activity of prenylflavonoids (2003) Fitoterapia, 74, pp. 720-724; Gibbons, S., Mathew, K.T., Gray, A.I., A caffeic acid ester from Halocnemum strobilaceum (1999) Phytochemistry, 51, pp. 465-467; Haraguchi, H., Yoshida, N., Ishikawa, H., Tamura, Y., Mizutani, K., Kinoshita, T., Protection of mitochondrial functions against oxidative stresses by isoflavans from Glycyrrhiza glabra (2000) Journal of Pharmacy and Pharmacology, 52, pp. 219-223; Kang, S.S., Kim, C.M., Korean indigenous plants. Part 2. Isolation of 1-eicosanyl caffeate from Echinosphora koreensis (1987) Archives of Pharmacal Research, 10, pp. 67-68; Kisiel, W., Jakupowic, J., Long chain alkyl hydroxy cinnamates from Crepis taraxacifolia (1995) Planta Medica, 61, pp. 87-88; Liu, W., Okajima, K., Murakami, K., Harada, N., Isobe, H., Irie, T., Role of neutrophil elastase in stress-induced gastric mucosal injury in rats (1998) Journal of Laboratory and Clinical Medicine, 132 (5), pp. 432-439; Okada, K., Tamura, Y., Yamamoto, M., Inou, Y., Takagaki, R., Takahashi, K., Identification of antimicrobial and anti-oxidant constituents from licorice of Russian and Xinjiang origin (1989) Chemical & Pharmaceutical Bulletin, 37, pp. 2528-2530; Repetto, M.G., Llesny Braz, S.F., Antioxidant properties of natural compounds used in popular medicine for gastric ulcers (2002) Journal of Medical and Biological Research, 35, pp. 523-534; Vani, T., Rajini, M., Sarkar, S., Shishoo, C.J., Antioxidant properties of the Ayurvedic formulation - Triphala and its constituents (1997) International Journal of Clinical Pharmacology Research, 35, pp. 313-317; Vaya, J., Belinky, P.A., Aviram, M., Antioxidant constituents from licorice roots: Isolation, structure elucidation and antioxidative capacity towards LDL oxidation (1997) Free Radicals in Biology & Medicine, 23, pp. 302-313",
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Dey, S, Deepak, M, Setty, M, D'Souza, P, Agarwal, A & Sangli, GK 2009, 'Bioactive caffeic acid esters from Glycyrrhiza glabra', Natural Product Research, vol. 23, no. 18, pp. 1657-1663. https://doi.org/10.1080/14786410802134348

Bioactive caffeic acid esters from Glycyrrhiza glabra. / Dey, S.; Deepak, M.; Setty, M.; D'Souza, P.; Agarwal, A.; Sangli, G.K.

In: Natural Product Research, Vol. 23, No. 18, 2009, p. 1657-1663.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Bioactive caffeic acid esters from Glycyrrhiza glabra

AU - Dey, S.

AU - Deepak, M.

AU - Setty, M.

AU - D'Souza, P.

AU - Agarwal, A.

AU - Sangli, G.K.

N1 - Cited By :11 Export Date: 10 November 2017 CODEN: NPRAA Correspondence Address: Deepak, M.; RD Centre, Natural Remedies Pvt. Ltd., Bangalore, India; email: deepak@naturalremedy.com Chemicals/CAS: 1,1 diphenyl 2 picrylhydrazyl, 1898-66-4; 2,2' azinobis(3 ethylbenzothiazoline 6 sulfonic acid), 28752-68-3; acetic acid, 127-08-2, 127-09-3, 64-19-7, 71-50-1; gallic acid, 149-91-7; methanol, 67-56-1; ursolic acid, 77-52-1; water, 7732-18-5; Antioxidants; Caffeic Acids; Enzyme Inhibitors; Esters; Pancreatic Elastase, 3.4.21.36; Plant Extracts; caffeic acid, 331-39-5 References: Auddy, B., Ferreira, M., Blasina, F., Lafon, L., Arredondo, F., Dajas, F., Screening of antioxidant activity of three Indian medicinal plants, traditionally used for the management of neurodegenerative diseases (2003) Journal of Ethnopharmacology, 84, pp. 131-138; Bafna, P.A., Balaraman, R., Anti-ulcer and anti-oxidant activity of pepticare, a herbomineral formulation (2005) Phytomedicine, 12, pp. 264-270; Beith, J., Spiess, B., Wermuth, C.G., The synthesis and analytical use of a highly sensitive and convenient substrate of elastase (1974) Biochemical Medicine, 11, pp. 350-357; Belinky, P.A., Aviram, M., Fuhrman, B., Rosenbat, M., Vaya, J., The antioxidative effects of the isoflavan glabridin on endogenous constituents of LDL during its oxidation (1998) Atherosclerosis, 137, pp. 49-61; Borrelli, F., Izzo, A.A., The plant kingdom as a source of anti-ulcer remedies (2000) Phytotherapy Research, 14, pp. 581-591; Fukai, T., Satoh, K., Nomura, T., Sakagami, H., Preliminary evaluation of antinephritis and radical scavenging activities of glabridin from Glycyrrhiza glabra (2003) Fitoterapia, 74, pp. 624-629; Fukai, T., Satoh, K., Nomura, T., Sakagami, H., Antinephritis and radical scavenging activity of prenylflavonoids (2003) Fitoterapia, 74, pp. 720-724; Gibbons, S., Mathew, K.T., Gray, A.I., A caffeic acid ester from Halocnemum strobilaceum (1999) Phytochemistry, 51, pp. 465-467; Haraguchi, H., Yoshida, N., Ishikawa, H., Tamura, Y., Mizutani, K., Kinoshita, T., Protection of mitochondrial functions against oxidative stresses by isoflavans from Glycyrrhiza glabra (2000) Journal of Pharmacy and Pharmacology, 52, pp. 219-223; Kang, S.S., Kim, C.M., Korean indigenous plants. Part 2. Isolation of 1-eicosanyl caffeate from Echinosphora koreensis (1987) Archives of Pharmacal Research, 10, pp. 67-68; Kisiel, W., Jakupowic, J., Long chain alkyl hydroxy cinnamates from Crepis taraxacifolia (1995) Planta Medica, 61, pp. 87-88; Liu, W., Okajima, K., Murakami, K., Harada, N., Isobe, H., Irie, T., Role of neutrophil elastase in stress-induced gastric mucosal injury in rats (1998) Journal of Laboratory and Clinical Medicine, 132 (5), pp. 432-439; Okada, K., Tamura, Y., Yamamoto, M., Inou, Y., Takagaki, R., Takahashi, K., Identification of antimicrobial and anti-oxidant constituents from licorice of Russian and Xinjiang origin (1989) Chemical & Pharmaceutical Bulletin, 37, pp. 2528-2530; Repetto, M.G., Llesny Braz, S.F., Antioxidant properties of natural compounds used in popular medicine for gastric ulcers (2002) Journal of Medical and Biological Research, 35, pp. 523-534; Vani, T., Rajini, M., Sarkar, S., Shishoo, C.J., Antioxidant properties of the Ayurvedic formulation - Triphala and its constituents (1997) International Journal of Clinical Pharmacology Research, 35, pp. 313-317; Vaya, J., Belinky, P.A., Aviram, M., Antioxidant constituents from licorice roots: Isolation, structure elucidation and antioxidative capacity towards LDL oxidation (1997) Free Radicals in Biology & Medicine, 23, pp. 302-313

PY - 2009

Y1 - 2009

N2 - Thin layer chromatography bioautography (using DPPH spray reagent) guided fractionation of Glycyrrhiza glabra led to the isolation of two caffeic acid derivative esters, viz. eicosanyl caffeate (1) and docosyl caffeate (2). The two compounds exhibited potent elastase inhibitory activity, with IC50 values of 0.99μg mL-1 and 1.4μg mL-1 for 1 and 2, respectively. The compounds also showed moderate antioxidant activity in DPPH and ABTS scavenging assays. The results indicate a possible role of caffeic acid derivatives, in addition to flavonoids in the anti-ulcer properties of G. glabra.

AB - Thin layer chromatography bioautography (using DPPH spray reagent) guided fractionation of Glycyrrhiza glabra led to the isolation of two caffeic acid derivative esters, viz. eicosanyl caffeate (1) and docosyl caffeate (2). The two compounds exhibited potent elastase inhibitory activity, with IC50 values of 0.99μg mL-1 and 1.4μg mL-1 for 1 and 2, respectively. The compounds also showed moderate antioxidant activity in DPPH and ABTS scavenging assays. The results indicate a possible role of caffeic acid derivatives, in addition to flavonoids in the anti-ulcer properties of G. glabra.

U2 - 10.1080/14786410802134348

DO - 10.1080/14786410802134348

M3 - Article

VL - 23

SP - 1657

EP - 1663

JO - Natural Product Research

JF - Natural Product Research

SN - 1478-6419

IS - 18

ER -